The lawsuit, filed Monday, alleges the police officers fired at Paul O'Neal "without lawful justification or excuse."
It's the latest shooting to highlight the already tenuous relationship between some communities and police, and it touches on broader issues that have time and again racked the Windy City: body cameras, police accountability and seemingly unstemmable violence.
Many in the nation's third-largest city are still reeling from the 2014 Laquan McDonald shooting, which left a Chicago officer facing a murder charge after more than a yearlong delay in releasing dashboard camera footage. And earlier this year, a task force established by the mayor released a report accusing the police of widespread racism.
O'Neal, 18, was shot Thursday and died from his injuries after leading a police chase through the South Side of Chicago. He had been suspected of stealing a car.
The body camera of the Chicago police officer who fatally shot O'Neal did not record when he opened fire, department spokesman Anthony Guglielmi said Monday.
On Tuesday, he said the officer who killed O'Neal was in a car that was struck by the car driven by O'Neal.
Whether the crash had an impact on the camera's ability to record is under investigation, he said. Investigators are also looking into whether the officer had turned it on.
Officers had received their body cams within the previous eight to 10 days, Guglielmi said. "We are currently in a pilot program," he said.
New police superintendent has questions, too
Chicago Police Superintendent Eddie Johnson told reporters the shooting troubled him, and he has relieved three officers of their police powers in connection with the shooting.
"Having been in shootings and car chases myself, I know how quickly you have to make those decisions," he said. "So if it's an honest mistake, we'll get them training, coaching, mentoring and get them back out there. But if it was intentional misconduct, then they have to be held accountable for it."
Though he cautioned he had not come to any firm conclusions, Johnson said the shooting had left him with "more questions than answers."
"As it appears right now, departmental policies may have been violated during the incident," he said.
Johnson was named the police superintendent in April
after serving as interim leader. Many viewed his appointment as a bid to stem a wave of violence in Chicago and to clean up a troubled department.
Lawyer questions why body cam didn't record
The chase began Thursday when officers tried to pull over a Jaguar S-type convertible reported stolen, according to the original police statement.
The driver tried to flee and sideswiped a police cruiser and another car parked near the scene, which "prompted two officers to discharge their weapons" while other patrol cars continued the chase, the statement said.
A third officer got out of a car and fired what was believed to be the fatal shot, according to CNN affiliate WLS.
Video from the body camera, had it been recording, may have provided critical evidence in the shooting.
The two officers whose car was struck head-on were treated and released from a hospital, officials said.
Police cannot legally shoot fleeing suspects unless they pose a threat to an officer's life or unless the officer has a good faith belief the suspect poses a substantial danger to the public.
Michael Oppenheimer, the O'Neal family attorney, questioned why the body camera had not functioned in the key moment.
"The police department is now saying that these brand new body cameras, that are supposed to save the world and give the police and the public transparency, did not work," he said at a Monday press conference. "We have also heard that the police department or the police took off their body cams or disconnected them."
He added, "When all of a sudden, there is a police shooting where they execute a kid in the back of the head, who is unarmed, how convenient that they don't work?"
Chicago's policing woes
Deep-seated distrust of law enforcement continues to plague relations between police and some Chicago communities.
In 2014, Laquan McDonald, a black teen
who was walking away from officers with a knife in his hand, was shot 16 times by a police officer. It took more than 400 days for the release of the dashboard camera footage of that shooting. The officer, Jason Van Dyke
, is facing murder and misconduct charges, and has pleaded not guilty.
The Police Accountability Task Force, created by Chicago Mayor Rahm Emanuel, released a scathing rebuke in April, accusing the police department of institutional racism and describing its accountability system as broken.
At the same time, Chicago has been rocked by violent crime. The city had 65 homicides in July alone, with 362 shooting incidents and 441 shooting victims, according to the Chicago Police Department.